


Fair and Square

by Pineprin137



Category: Supernatural
Genre: Brotherly Love, Dean Winchester Whump, Desperation, Emetophilia, Food Kink, Hurt/Comfort, M/M, Mildly Dubious Consent, No actual sex between the brothers, Not literally, Omorashi, Public Masturbation, Right?, Sadistic Sam Winchester, Vomiting, Wincest - Freeform, because that's a thing, in a good way, they just get off on each other
Language: English
Status: Completed
Published: 2019-04-28
Updated: 2019-04-28
Packaged: 2020-02-09 07:36:29
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 3,508
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18633709
Author URL: https://archiveofourown.org/users/Pineprin137/pseuds/Pineprin137
Summary: Sam wins a wager and exacts his little brother revenge. Because after all, a bursting big brother makes for a very happy Sam.





	1. Desperate Times Call for Desperate Measures

**Author's Note:**

> Trigger Warning for vomit. It's only in chapter two but, the depictions are somewhat graphic.

Sam turned the wheel sharply and smirked at his big brother’s wince. Dean had been clutching himself for the last one hundred and fifty miles and now began to bounce. He hid his smile and glanced at the man next to him. “You gonna make it, big brother?” Dean didn’t even spare him a glance, instead, he leaned forward till he was almost double and for a second Sam worried he might throw up instead of piss himself. “Dean? You okay?” Sam watched as Dean bit down hard on his lip and started rocking. But it didn’t take long before he changed position again and returned to staring at the roof of the Impala with his fists pushing against his jean-clad thighs. Sam tore his eyes away from his miserable brother and searched for somewhere to pull over. The desperation was hot, but seeing his brother in legitimate pain killed any lust that simmered deep in Sam’s gut.  

“Sammy?” Dean barely whispered his name. He had one hand clutched tightly against the crotch of his jeans and the other gripping the leather seat so hard Sam feared it may tear. Dean would be pissed if their little bet warranted an emergency patch job. Well, not the actual bet, rather the punishment. Sam had won fair-and-square so Dean had to do whatever he said for twenty-four hours. It was almost nine now so he still had another eight hours of control left. He had blocked Dean’s trip to the men’s room last night and informed him he had to hold it until Sam said he could go. His drunk brother had laughed at first, thinking it was a joke, but sobered when he saw Sam’s smirk. Dean had tried to find a loophole by not ordering more beers, but Sam just got him water instead. Refilling the glass over and over till Dean said he would puke if Sam made him drink anymore. Which he had proven on the walk back to the motel. 

“Hang on, Dean. I’m looking for somewhere to pull over. Just hold on a little longer, okay?” He finally spotted a small dirt shoulder a little further up the road and tried to calculate the possibility of Dean making it till there without wetting himself. The older Winchester was now moaning full-out and switching between rocking and holding still while he fought for control. “Half a mile, kay? Almost there.” 

“Fuck. I don’t know how much longer I can hold it. Hurry, Sam.” One leg was shaking and his right fist was clenched around the door handle. “Shit. Sammy, I don’t think I can make it. You gotta stop, man. Now. ” Sam didn’t say anything just pushed the pedal down a little harder. They were only two hundred feet away. 

“Two minutes, Dean. You can do it.” He heard the sound of a zipper and pulled to the side just as Dean pulled his cock free and swung the door open. Sam put the car in Park and then walked around to check on his brother. Dean was leaning against the Impala as he finally gave in and released his aching bladder. Sam was frozen, hearing his brother’s relieved moan. He also caught sight of Dean’s hand stroking his dick as he pissed into the dirt. They stood there for over a minute, Dean moaning with his eyes closed and Sam blatantly watching him while he rubbed a hand against his fly, before the stream finally let up and Dean’s head laid back on Baby’s roof. He was panting so hard Sam wondered if he would see cum mixed into the piss at his brother’s feet if he dared look down. 

Dean let out a long breath and then smiled in Sam’s direction without opening his eyes. “Holy shit, that felt good.” He managed a deeper breath and then met Sam’s amused gaze. “What?” Sam didn’t answer just looked down to where Dean’s cock still hung out of his jeans. A blush spread over his brother’s cheeks as he tucked himself back in and zipped up. 


	2. Glutton For Punishment

**Summary for the Chapter:**

> Fun's not over yet...

**Notes for the Chapter:**

> This chapter is mostly emetophilia and food kink, but there is a little hinting at more desperation. Dean just can't catch a break.

It was a little after eleven when they pulled into a diner for lunch. Dean was still a bit embarrassed by what happened earlier, but Sam had let him drive so he was doing better. He had grimaced when Sam started handing him more bottles of water to drink, but dutifully chugged them down one by one only pausing to belch against his fist. Dean’s bladder was nice and swollen, but Sam wanted something else this time. His brother was a glutton, so he had no trouble convincing Dean to pull over at the diner for an early lunch. The only catch was that Sam would order and Dean would have to eat whatever he chose. His older brother had actually rolled his eyes at his “threat”. Dean wasn’t worried about eating, he loved food. 

An hour and a half later Dean was cursing that statement. Sam had ordered one of everything off the menu and although it was a small menu, thank God, Dean was feeling a little overwhelmed and a lot stuffed. He had already worked his way through two omelets, a stack of pancakes, an open-faced roast beef sandwich with mashed potatoes and gravy, a small side salad, a Heartland special containing scrambled eggs, bacon, sausage, and home fries, and now he was staring down four pieces of pie. One cherry, one blueberry, and two apple because the waitress had insisted. Dean loved pie. Almost as much as he loved Baby and Sam, but right now he would give anything to leave his favorite food untouched. He clenched his jaw as his stomach groaned. 

“C’ mon, Dean. It’s only four small slices. I’ve seen you take down twelve easy. And there’s even cherry. You never turn down cherry pie.” It was true. Cherry pie was his favorite and usually, he would’ve already wolfed it down, but right now just thinking about making room in his stomach for it was nauseating. 

“Yeah. But I hadn’t just eaten an entire buffet of breakfast foods. Sam, can’t we just go? I’m already full.” Sam watched his brother rub a hand over his round stomach. It was protruding enough that Dean had already released the top button of his jeans and had his legs spread wide to make room in the booth. His brother groaned and brought a fist up to his mouth so he could belch into it. Dean swallowed the aftertaste of slightly burnt meat mixed with greasy starch when Sam slid the cherry slice directly in front of him. 

“Okay, how ‘bout you eat just one then?” Sam laid his hand on top of his brother’s where it rested on the table. “For me?” Dammit. Dean was no match for his brother’s puppy dog eyes. Sam smiled when Dean picked up the fork and cut a big bite. He hesitated for a minute, licking his lips before bringing the loaded fork to his mouth. Dean grimaced slightly as he chewed and it took two tries for him to swallow, but he managed. Sam watched as his brother alternated between rubbing his swollen belly, taking a bite of pie, and then sipping from his glass of water. He smiled encouragingly at Dean across the booth and nodded to the remaining bite on the small plate. Dean sighed at Sam and then glanced down to the almost-empty plate in front of him. One more bite. He could do this. He could eat one last fucking piece of flaky crust covered in cherry-flavored goo for the satisfaction of his slightly sadistic brother. 

Dean didn’t waste any more time. He speared it with his fork and shoved it into his mouth before he could wimp out. Sam’s eyebrow lifted at his ferocity, but at this point, all Dean could focus on was forcing the last bite down his gullet to join the mess of other foods in his grumbling belly. As soon as it traveled into his throat it wanted to come back up. Sam watched his brother swallow hard and then slowly breathe through his nose. His jeans were starting to get tight across his groin now that he knew Dean was close. His risked palming himself under the table when his big brother turned to the side and gagged against his fist. He coughed a few times before he finally lifted his head to meet Sam’s eyes.

Dean didn’t miss the movement of his brother’s hand underneath the table and his body decided to respond. He winced as his dick filled and pushed up against his full belly. He could feel the sweat starting to drip down his back and trail along his hairline. He pleaded with his brother through teary eyes. All he wanted was to get out of here, back to the bunker, and lie down on his memory foam with a bucket by his head so he could be miserable in private. 

Sam nodded, grabbed the ticket off their table, and headed to the register to pay. Dean slowly eased himself from the booth and tried to stand. He couldn’t quite straighten out all the way and the movement caused his abdomen to twinge as his bladder reminded him of all the water Sam made him drink. He felt like a pregnant woman as he waddled towards the men’s room. He caught several concerned glances from the other diners and one elderly couple even asked him if he was okay. He managed a small smile in their direction before pushing open the door and making his way to a stall. He automatically started hiccupping when his stomach realized where he was and urged him to kneel in front of the toilet, but he just ignored it and fumbled with his zipper for the second time that day. 

“Dean? You alright?” He heard his brother’s footsteps come up to the stall door just as he let go. Sam chuckled when Dean moaned while emptying his bladder. The sound of his brother’s relief reminded Sam that he hadn’t gone in a few hours so he stepped into the next stall and took care of business as well. Dean’s stream had slowed to a trickle, but now his stomach was churning angrily. He was trying to decide whether or not to just get it over with when he was distracted by the sound of someone grunting and beating their meat. He looked to his left and imagined Sam jerking off just a few feet from him. Sam leaned forward with one hand against the wall, the other busy stroking his stiff cock. Just the thought of Dean’s desperation and the image of his swollen middle had done him in. He bit his lip as heard his brother cough and sped up his fist. 

Dean swallowed, but then doubled over with a rough hiccup that turned into a deep cough. Oh god. He was going to lose it right here in the grungy bathroom of a diner in some no-name town while his brother got off on his misery not even five feet from him. His stomach gave a loud gurgle and then flipped. “Ugh.” He hung his head and let the drool fall from his mouth into the piss-filled bowl. He lurched forward with a gag, but nothing came up. It was Dean’s first gag that sent Sam over the edge. He jerked, shot his load into the bowl of dirty water, and then stroked himself through the aftershocks while his brother fought the impending sickness. Sam flushed the evidence and washed his hands quickly before walking back over to the stall Dean was in. He noticed the door wasn’t latched all the way so he pushed it open and stood just behind his brother. 

Dean felt Sam’s hands on his back and he wanted to cry with relief, but his belly was still full and although he had been gagging while Sam cleaned up, he hadn’t actually brought anything up yet. “Ugh, Sammy.” Sam took pity on the miserable man standing in front of him and as soon as he felt Dean’s back contract with another retch he pushed against his brother’s swollen belly. Dean barely felt the press of Sam’s warm hand, but the effect was instant. Dean pitched forward and a wave of vomit spilled into the toilet. He only had a moment to catch his breath before another gush of undigested food forced its way back up. After a few minutes of non-stop sickness, he leaned back against Sam and gasped for much-needed air. 

Sam supported Dean while he took advantage of a breather in between rounds of vomiting. He could still feel the tightness of Dean’s muscles so he had a feeling they weren’t done yet. Dean groaned when another wave of nausea passed over him and he reluctantly resumed his position over the bowl. Sam quickly reached down and flushed so his brother wouldn’t have to stare at his former meal. A moment later Dean gripped the toilet seat and heaved up a chunky wave of what must have once been pancakes. He coughed roughly to clear his throat and then spat out another mouthful of creamy liquid. “Oh god, make it stop. Ugh, Sammy, make it…” Dean was interrupted by a harsh gag that jerked both brothers closer to the water. Sam held him as the dry heaving began and shushed him gently. Dean whimpered and grasped Sam’s hand, pulling it up to his mouth and pressing the digits against his sticky mouth. 

“Are you sure?” Dean responded by slipping Sam’s fingers through his parted lips and sliding them along his tongue. Dean released his hand when Sam took over. Pushing against the back of his brother’s throat and then stroking his soft palate. Dean gagged, but still only drool spilled from his lips. Sam leaned over his brother so they were back to front and wrapped his free hand around Dean’s, much smaller, abdomen. This time when he tickled Dean’s gag reflex, he also pushed into the soft flesh just under his brother’s faded tee-shirt. That did it. Dean tried to hold back until Sam’s hand was clear, but the vomit surged up his throat too fast and his brother’s hand was covered in the liquid remains of their meal. 

Dean coughed a few times to clear his throat while Sam reached around and flushed the toilet again. Then he pulled some toilet paper off the roll and turned Dean around so he could clean him up. Once Dean’s face and hands were wiped off, he flushed a third time and then led him to the row of sinks. Sam guided his brother’s hands under the water so he could rinse out his mouth and then wet his fingers to smooth back Dean’s sweaty hair. His brother wouldn’t meet his eyes, so Sam grabbed his chin and forced his head up. “Hey, talk to me. What’s wrong?” Dean averted his gaze again and mumbled something Sam couldn’t make out. “What? I can’t hear you when you’re talking to the floor.” He continued to run one hand through Dean’s messy hair and rested the other on his shoulder. 

Dean huffed out a breath and looked Sam directly in the face. “I said I think we’re going to have to do laundry when we get back.” He glared when Sam laughed. “It’s not funny, Sam. This was my last clean pair of jeans.” Sam saw his brother squirm and finally caught on. Sure enough, when he looked down at Dean’s crotch, he saw a slight discoloration that hinted that Dean had enjoyed the process of emptying his stomach more than he let on. 

“Dean. It’s okay. I remember seeing a pair of sweatpants in the trunk. You can change in the car.” 

“Thanks, Sammy.” He nodded as Dean dried off his hands on his dirty jeans and then wrapped an arm around his big brother’s waist as they walked out of the restaurant. 

“Hey, Sam?” He glanced at his brother and cocked an eyebrow. “What time did we leave the bar?” Sam couldn’t help the laughter that erupted out of him. He had to stay bent over for a few minutes till he caught his breath. Dean crossed his arms and rolled his eyes at his little brother. When Sam finally rose, he checked Dean’s watch and answered, “You still have five hours left.” Dean groaned where his head was lying against Sam’s chest. “Let’s see...Dean, I want you to...pull into the nearest motel above a two-star rating and pick out some movies for us to watch.” Sam looked down to see Dean’s surprise and smiled before continuing, “I think maybe you’ve suffered enough for today, now it’s time to relax and recuperate. What do you say?”

Dean smirked up at him before pulling away and walking towards the Impala. “I say you’re on.” 


	3. Prologue

**Summary for the Chapter:**

> Dean gets a little too cocky and Sam puts him in his place.

**Notes for the Chapter:**

> This is the night of the bet, so it actually comes before chapter one chronologically.

Dean took a long drink from his sixth or seventh beer, he had lost count and watched his little brother hit the wall with another dart. “Dude, you look like you’ve never played before. Are you seriously that drunk?” 

“Shut up, Dean. You’re way drunker than I am.” Dean arched an eyebrow at him. Drunker? Sammy was definitely on his way to wasted. Besides, Dean could tolerate liquor a lot better than his little brother. Drinking went hand in hand with hunting. Not deer hunting, monster hunting. Not during the hunt, but after you ganked it and uh sometimes before too like during research. Huh. Maybe that  _ had _ been his seventh beer. He chuckled when Sam missed the board yet again. This one didn’t even make it to the wall, just fell to the floor in a limp arc. 

“Okay, hot stuff, step aside and let the master show you how it’s done.” Dean frowned and chugged the rest of his beer. Did he just call his brother hot stuff in a crowded public space? Surely, he was mistaken. Or Sam was right and he  _ was _ way drunker. He stood up from the table and the room spun for a moment. He burped into his fist and then motioned to Sam to give him the darts. Sam looked at the drunken fool swaying in front of him and grinned to himself. 

“Alright, alright, here. If you say you're the master, then I suppose I can’t argue.” 

“Damn straight.” He glared when Sam kept moving his hands, but finally snagged the darts and walked over to the line. Sam chuckled when Dean missed his hand three times and then bumped into a table. Sam leaned carefully against the table and watched Dean try to line up his shot. 

“Hey, Dean. How about we make this...interesting.” Dean grinned at him and crossed his arms, almost stabbing himself with the darts. Sam winced and shook his head at his idiot brother. Dean lived for challenges, especially the ones issued by his brother. And right now with several cold beers in his belly, he was putty in Sam’s hands. 

“Whatch’ya have in mind, Sammy?”

“How ‘bout one round? The winner earns the right to command the other for a whole day.” He watched as Dean considered the offer and his palms started to sweat. One whole day of telling his big brother what to do? That was every little brother’s wet dream. Speaking of wet, that gave him an idea. 

“Okay, Sammy. You’re on.” Dean gave him a smirk and then spun back towards the board. He stood still for a moment to wait for the room to stop spinning and then raised his arm.   

Sam watched as his brother threw two darts into the wall surrounding the board and then misthrew the last one and it drifted to the floor. He allowed Dean a re-do and smirked when it landed in someone’s beer  _ behind _ them. Dean started growling at the board and complaining about uneven floors so Sam took the opportunity to count the bottles littering their table. There were thirteen empty bottles of El Sol on the table and Sam had only finished three which meant Dean was officially drunk. It was a rare occasion to see his brother shitfaced since he had such a higher alcohol tolerance compared to Sam.

Dean scowled and made his way back to the table where he collapsed into his chair and drank half of Sam’s untouched fourth beer. Sam gathered up the darts and took a breath before walking up to the line and lining up his shot. He sunk the first one in the bull’s eye and heard a groan come from behind him. He chuckled and threw the rest haphazardly. It didn’t matter where they landed, the bull’s eye meant he won. Dean’s head hit the table with a thunk when he realized he was going to be his little brother’s slave for the next twenty-four hours. Sam caught the moment of comprehension on his brother’s face and wished he had a camera. This was going to be fun. 


End file.
